Category: gonewildstories

One of my biggest fantasies fulfilled, almost too easily [MT]

First off, this was a hook-up with a trans girl, if that doesn’t get you off, stop reading now.
I have always had a kink for passable trans girls, not at all interested in men or “sissies”.
This was only 3 days ago and I’m still trying to decide my next move. She told me she is on Reddit but wouldn’t give me her username…

So I’ll begin with how this started over a week ago.
I was having a conversation with a friend at work, she’s basically my best platonic friend, I share everything with her and her to me. We’ve never fooled around or anything, we’ve made jokes about fucking but never have, surprisingly.
Anyway, I told her I had a fantasy for trans girls, and it took me a few drinks to say it, as in I almost immediately regretted it.
She got this smirk on her face and started texting someone, I got on the defence and told her to keep it to herself but she basically told me to shut up and wait.
Long story short, her sister’s best friend is a trans girl that was looking for a hook-up, and she gave me her number.
I played it off like maybe I would think about calling her, but after 2 days it was all I could think about. I was jerking off to girls on r/traps and feeding the fire, so I texted her a “hey”.
She texted back within minutes
“Hi!, I’ve been waiting for a text ;)”
(Let’s call her Chrissy as I doubt she would want her real name shared) Read more »

[MF] Fun Hookup Night (Part 2)

I was softly running my hands over her now fully naked body when she opened her eyes, looked at me, and said “I know what I want us to do next.” “Oh, really?” I responded both curious and excited. “The next thing we’re going to do…” and then she paused for a few seconds, “…is you’re going to do anything you want to me.” My eyes got big when she said that and of course it excited me. I jokingly responded, “You sure about that?”. She giggled and said “Try, me.”

I pretended to think it over for a little bit, but I already knew what I wanted to do. After my pause, I said “I want to eat your ass”. When I said that, Mel kind of recoiled just a little bit and said, “Like my butthole??” And I said, “yep, like especially your butthole.” Mel was still not sure what to make of my request and said, “You’re serious? I can kind of understand why you would want to lick my vagina, but how is licking my butt at all enjoyable for you?”. Read more »

[MF] Fun Hookup Night (Part 1)

This is a story of a hookup I had many years ago when I was a year or two out of college. There’s nothing particularly noteworthy about it other than it was a really fun night that still turns me on to this day to think about, so I thought I would share it here. It’s a true story, at least as best that I can remember it.

Before I begin with the night in question, I thought I’d give you a brief overview on where I was coming from. I was always a pretty horny kid. My adolescence lined up with the early years of the internet, so once I discovered internet porn, I became pretty fascinated with all things related to sex or the female body. Growing up, I remember my friends all boasting about how hot various women like Pamela Anderson were and how amazing it would be to fuck someone like that, but I never felt that way. And this is in no way a dig at Pam Anderson, but I always got turned on by women that seemed real. Even in the early days of internet porn when there wasn’t a huge selection, I always searched out amateur type porn. I got way more turned on by some ordinary college girl or a naked housewife than any celebrity, model or porn star. And I also hardly ever fantasized about fucking. The number one thing I dreamed about doing to a girl was to eat her out. But I also fantasized about just examining her. Getting to see what her boobs, nipples, and especially her pussy looked like up close. And getting to lick her would be the ultimate way of experiencing every part of her, which is why it always seemed so appealing and sexy. More than anything I was just so fascinated and curious with the female body, and I definitely thought about it a lot. Read more »

Freeuse Slut for his housemates [F]

I am seeing this boy at uni who lives in private accommodation
with his housemates. Whenever I go to his place, he sort of plays with me in the living room or in the kitchen, basically in the open a lot. He lives with 3 other boys who are also fairly good looking. Anyways once they were all playing Fifa and I was sitting beside him when he reaches down my shorts and is playing with my ass. Then his friends were there and they asked if they could also fool around, since they were horny. So we both said yes and we all fooled around. It eventually turned into a gangbang, and I was on the couch having a threesome with 2 of them, while another 2 were jerking off on the side awaiting their turn.
Since that event, I’m basically a free use slut whenever I go to their house. As soon as I walk in, I get felt up by whoever is home, and then even if I’m sitting there studying, they’ll come and put their dick into one of my holes.
The other day, I was tied up on one of the beds and gagged and they all simply took turns until they had emptied their balls and were ready to untie me.

4th of July Fun (MILF) [MF]

I have a mature aged co worker. She’s 20 years my senior. She’s never been married or had kids. She was in her early 20’s during the late 70s/ early 80s so she partied hard!

From the drunken nights at our office parties I’ve heard all the stories.

She partied with Joe Pesci at the race track, she blew Steven Tyler backstage at the Hollywood bowl, she even got spit roasted by Mick Jagger and his tour manager. All the while being coked out of her head for a decade.

Those days are behind her now. She is really fun and perky and kind to everyone. She doesn’t have any family so she see’s the office as more of a social setting then a work place, so she lets her guard down, acting like we’re all schoolmates rather than co workers.

We innocently flirt from time to time. Giving her some attention to keep her happy. Harmless fun.

We just had a potluck for 4th of July last Friday and they let us drink! So of course, she had a heavy hand and had drunk half a bottle of wine before desert. Read more »

I [M] got paid to suck off a gay couple [MM].

In my late 20s I was finding [myself](https://www.reddit.com/user/sapsford4013/comments/ns09lh/im_letting_my_chest_hair_grow_hows_does_it_look/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) and experimenting with bi sex.

As part of process, I used hook-up websites to meet older bi/gay men. I hit it off with a mid-50s guy. I’ll call him Bottom. After meeting for a quick coffee, we ended up back at his nearby apartment for some light-hearted fun — making out and mutual cock sucking. I was very very new to bi play, so I didn’t intend to rush into anything. He asked for me to take his ass, but at the time the thought did not appeal to me so I declined. We both ended up coming on each other’s chest.

Afterwards, he asked for me to stay a while longer to meet his partner. I’ll call him Top. I told him I couldn’t. He offered $200 as an incentive to stay. It worked.

Top arrived home, we met and a brief conversation. I wasn’t physically attracted to him, but I knew now I’d have to play with him as well because I’d been paid — I felt compelled. Read more »

Fun night with girlfriend and her sister (sexual content) [FMF]

Sorry if this is too long, this is my first time posting one of my past experiences, I hope you like it. Throwaway account as I wish to remain anonymous to casual viewers.

My GF (20F, let’s call her Sophie) and my GF’s straight sister (19F, let’s call her Poppy) are very close and have been eachothers best friends their whole life. They both look quite similar, with athletic bodies and are both quite short. Throughout our relationship, Poppy has always been really close and involved in our relationship to the point where we hang out a lot, have all see eachother naked before and talk about anything together. Me (20M, straight, in good shape) and Sophie are both really open about sex and love showing ourselves off when we’re drunk/high to our closest friends. Me Sophie and Poppy are all very close, and do MDMA together sometimes where we all become very ‘comfortable’ together.

The last few times where we have done md together, Sophie and Poppy usually like comparing their arses (as they’ve just started working out their bums) so they usually end up taking their trousers off and asking me to take a picture of their bums together so they can compare them. Read more »

I 25 [f] want to make Daddy feel good

Felt I needed to share after seeing this hot dad at Home Depot today ;)

Anyway .. lol a little backstory.. I know dead bedrooms are a real problem for couples. I constantly hear about, and see the defeat and boredom surrounding long term, monogamous couples. (Not saying they are all like this, but enough are that it is a problem)

And although I love helping and playing with couples, I also love singling out; helping, and playing with hot daddies ;)

I’m a straight up tease ;) and I love it

I really enjoy wearing skimpy/slutty clothing to entice, and show daddies a hot little body they can then think about later with their wives. .

It’s such a turn on making eye contact with them, or noticing when they look at my ass and/or tits poking through my shirt. .

I often try to smile; bite my lip, bend over a little too often, and ask for their help finding something, in order to get their attention and show them I’m interested. Read more »

[F] Medical ASSistant

https://imgur.com/a/eiut42Y

I work at a women’s clinic as a medical assistant and when we see our patients they usually bring in their significant other to their appointments. My work uniform is scrubs obviously and well I’m not a big fan of the loose fit scrubs that hide my ass. So i wear tighter fit scrubs like a thin athletic material which hugs my ass in all the right places.

My co-workers have noticed more and more since I’ve been at this locations that some of the men or husbands who come in can’t stop staring at my ass and especially when I turn around and bend over. My scrubs can get a clear view of my panty lines. When I’m wearing a g string my ass eats the scrubs up. When I’m wearing a thong you can see the perfect triangle. When I’m wearing bootyshorts or a lace thong you can make out the lace from how tight my pants are. They aren’t see through but definitely thin enough get a good look of what I have on. I’ve been bent over a few times to turn around while my ass is up in the air and I can see them licking those lips or biting them. Some brave ones have even made bold comments like “dam you have a big ass” “those pants look really good on you” “ too bad my wife is here” all I do is smile and bend over again. Read more »

[M]y [F]irst Time being Pegged

It started as most evenings did with this girl.

I was on the bus home from work, sitting in traffic, and got the usual “you free tonight? :)” text.

It had been a long week, and we were just over the hump. I paused for awhile debating whether I had time when I got a second text: “I have bread :)”

She worked at a bakery in town, and knew that fresh baguette was my absolute weakness.

I responded “I have wine, see you around 7?”

I got back to my condo to get cleaned up and change out of my suit for something more casual. She always said the suits intimidated her, and not in a sexy kinky way.

I liked how simple and carefree she was. Tall but petite brunette. Thin with not a lot in the curves department, but with the cutest and perkiest A cups. She seldom wore bras and I loved it more than I could ever handle. She usually wore overalls covered in flour and paint, and she always seemed to me like someone too good for this world.

We also had the BEST sex. Read more »